1.2 Deoxyfluorination of Aliphatic Alcohols
Buch
Herausgeber: Paquin, J.-F.
Titel: Modern Strategies in Organofluorine Chemistry 1
Online ISBN: 9783132458253; Buch-DOI: 10.1055/b000000921
1st edition © 2024. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie
Science of Synthesis Reference Libraries
Übergeordnete Publikation
Titel: Science of Synthesis
DOI: 10.1055/b-00000101
Reihenherausgeber: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.
Typ: Mehrbändiges Werk
Abstract
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The selective incorporation of fluoroalkyl motifs into complex organic molecules represents a significant challenge in fluorine chemistry. Among the various methods allowing the synthesis of alkyl fluorides, the deoxyfluorination of aliphatic alcohols remains one of the most practical, especially because substrates are readily available. This transformation has been popularized by the use of diethylaminosulfur trifluoride (DAST) and N,N-bis(2-methoxyethyl)aminosulfur trifluoride (Deoxo-Fluor) reagents. However, the safety and chemoselectivity issues related to these reagents have led to the development of innovative reagents and protocols to perform this key reaction. This review aims to highlight the recent progress made in the field of deoxyfluorination of aliphatic alcohols and to provide the reader with useful guidelines with a view to performing such a transformation.